Issue 4, 2017
From the journal:

Organic & Biomolecular Chemistry

C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene†

Jack Emerson-King, ORCID logo a   Simone A. Hausera  and  Adrian B. Chaplin ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, UK
E-mail: a.b.chaplin@warwick.ac.uk
Web: http://go.warwick.ac.uk/abchaplin, http://www.twitter.com/chaplinlab

Abstract

The N-heterocyclic carbene IBioxMe4 enacts selective single and double C–F bond activation of octafluorotoluene and hexafluorobenzene, respectively. The formation of the fluoroarene substituted, zwitterionic imidazoliumolate products is consistent with a mechanism involving nucleophilic aromatic substitution and subsequent oxazoline ring opening by liberated fluoride.

Graphical abstract: C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C6OB02556K
Article type
Communication
Submitted
22 Nov 2016
Accepted
13 Dec 2016
First published
22 Dec 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2017,15, 787-789

Permissions

Request permissions

C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene

J. Emerson-King, S. A. Hauser and A. B. Chaplin, Org. Biomol. Chem., 2017, 15, 787 DOI: 10.1039/C6OB02556K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements